Oxindole → 3-Methyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (3-diethylaminopropyl)amide

HRID 1246092Notes

Reaction equation

HRID 1246092 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH2:11]([N:13]([CH2:28][CH3:29])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]1[NH:21][C:22]([CH:26]=O)=[CH:23][C:24]=1[CH3:25])=[O:19])[CH3:12].C(OC(C1C(C=O)(C)C=CN1)=O)C>>[CH2:28]([N:13]([CH2:11][CH3:12])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]1[NH:21][C:22]([CH:26]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:23][C:24]=1[CH3:25])=[O:19])[CH3:29]

Participants

4

Reactant 3

HCID 321710OxindoleHCID 865861965-formyl-3-methyl-1H-pyrrole-2-carboxylic acid (3-diethylaminopropyl) amideHCID 865861973-formyl-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 672809723-Methyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (3-diethylaminopropyl)amideYield 21%

Procedure

Oxindole (66.5 mg, 0.5 mmol) was condensed with 5-formyl-3-methyl-1H-pyrrole-2-carboxylic acid (3-diethylaminopropyl)amide (prepared from 3-formyl-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester by method B then C) to give 39 mg (21%) of the title compound.

Sources & evidence

ORD record
ord-c00d5d48574747a691dcd504b40ffab8
Source dataset
uspto-grants-2006_10
Patent number
US07125905B2

Reaction notes

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